TW318180B - - Google Patents
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- Publication number
- TW318180B TW318180B TW085104429A TW85104429A TW318180B TW 318180 B TW318180 B TW 318180B TW 085104429 A TW085104429 A TW 085104429A TW 85104429 A TW85104429 A TW 85104429A TW 318180 B TW318180 B TW 318180B
- Authority
- TW
- Taiwan
- Prior art keywords
- distillation
- ethylene sulfide
- distillation column
- patent application
- tower
- Prior art date
Links
- 238000004821 distillation Methods 0.000 claims description 287
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 claims description 256
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 122
- 150000002894 organic compounds Chemical class 0.000 claims description 102
- 238000000034 method Methods 0.000 claims description 100
- 230000002209 hydrophobic effect Effects 0.000 claims description 98
- 238000001944 continuous distillation Methods 0.000 claims description 80
- 238000011084 recovery Methods 0.000 claims description 49
- 238000000926 separation method Methods 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 39
- 238000010025 steaming Methods 0.000 claims description 37
- 238000006297 dehydration reaction Methods 0.000 claims description 34
- 238000010992 reflux Methods 0.000 claims description 34
- 238000009835 boiling Methods 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 230000018044 dehydration Effects 0.000 claims description 32
- 238000003860 storage Methods 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 27
- 238000011049 filling Methods 0.000 claims description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 11
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000002079 cooperative effect Effects 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 3
- 238000007639 printing Methods 0.000 claims description 3
- 238000009223 counseling Methods 0.000 claims description 2
- 238000006477 desulfuration reaction Methods 0.000 claims description 2
- 230000023556 desulfurization Effects 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 238000005486 sulfidation Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- MAHNFPMIPQKPPI-UHFFFAOYSA-N disulfur Chemical compound S=S MAHNFPMIPQKPPI-UHFFFAOYSA-N 0.000 claims 1
- 239000000779 smoke Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 80
- 239000000243 solution Substances 0.000 description 68
- 229920000642 polymer Polymers 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 24
- 239000011259 mixed solution Substances 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 14
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 9
- -1 alkyl mercaptan Chemical compound 0.000 description 8
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 150000003573 thiols Chemical class 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 230000019086 sulfide ion homeostasis Effects 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- 150000003544 thiamines Chemical class 0.000 description 2
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- ODVQJULKROKYBG-UHFFFAOYSA-N C1=CC=CC=C1.C1CS1 Chemical compound C1=CC=CC=C1.C1CS1 ODVQJULKROKYBG-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000009924 canning Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XSQNOFMFKVYSNL-UHFFFAOYSA-N ethene;toluene Chemical compound C=C.CC1=CC=CC=C1 XSQNOFMFKVYSNL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- RQIOMXQOMYOGKD-UHFFFAOYSA-N fluorocyclohexane Chemical compound FC1[CH]CCCC1 RQIOMXQOMYOGKD-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005242 forging Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000003761 preservation solution Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/146—Multiple effect distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8039695A JP2685730B2 (ja) | 1995-04-05 | 1995-04-05 | エチレンスルフィドの回収方法 |
| JP8563795A JP2685731B2 (ja) | 1995-04-11 | 1995-04-11 | エチレンスルフィドの脱水方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW318180B true TW318180B (enrdf_load_stackoverflow) | 1997-10-21 |
Family
ID=26421410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW085104429A TW318180B (enrdf_load_stackoverflow) | 1995-04-05 | 1996-04-13 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5833813A (enrdf_load_stackoverflow) |
| EP (1) | EP0764646B1 (enrdf_load_stackoverflow) |
| KR (1) | KR100211492B1 (enrdf_load_stackoverflow) |
| CN (1) | CN1149872A (enrdf_load_stackoverflow) |
| DE (1) | DE69628889D1 (enrdf_load_stackoverflow) |
| TW (1) | TW318180B (enrdf_load_stackoverflow) |
| WO (1) | WO1996031495A1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105999996A (zh) * | 2016-06-20 | 2016-10-12 | 保定加合精细化工有限公司 | 一种从废气回收环硫乙烷的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1135800A (enrdf_load_stackoverflow) * | ||||
| GB1051947A (enrdf_load_stackoverflow) * | 1964-09-18 | |||
| US3687976A (en) * | 1966-01-04 | 1972-08-29 | Exxon Research Engineering Co | Process for the preparation of cyclic sulfides |
| US3622597A (en) * | 1968-09-13 | 1971-11-23 | Dow Chemical Co | Method of preparing thiiranes from mercaptoalcohols |
| NL7001172A (en) * | 1970-01-28 | 1970-06-23 | Production of alkylene sulphides | |
| FR2136912B1 (enrdf_load_stackoverflow) * | 1971-05-07 | 1973-05-11 | Aquitaine Petrole | |
| IT956765B (it) * | 1972-06-22 | 1973-10-10 | Montedison Spa | Procedimento per la purificazione di 1 3 diossolano |
| US5304656A (en) * | 1991-11-29 | 1994-04-19 | Nippon Shokubai Co., Ltd. | Process for preparing alkylene sulfides |
| JP2537324B2 (ja) * | 1992-06-11 | 1996-09-25 | 株式会社日本触媒 | アルキレンスルフィドの捕集方法 |
| JP3164707B2 (ja) * | 1993-08-30 | 2001-05-08 | 三井化学株式会社 | １，３−ジメチル−２−イミダゾリジノンを回収する方法 |
| JPH0770097A (ja) * | 1993-09-02 | 1995-03-14 | Daicel Chem Ind Ltd | クロロスチレンオキシドの製造方法 |
-
1996
- 1996-04-02 KR KR1019960706841A patent/KR100211492B1/ko not_active Expired - Fee Related
- 1996-04-02 US US08/737,207 patent/US5833813A/en not_active Expired - Fee Related
- 1996-04-02 DE DE69628889T patent/DE69628889D1/de not_active Expired - Lifetime
- 1996-04-02 WO PCT/JP1996/000890 patent/WO1996031495A1/ja active IP Right Grant
- 1996-04-02 EP EP96907748A patent/EP0764646B1/en not_active Expired - Lifetime
- 1996-04-02 CN CN96190274A patent/CN1149872A/zh active Pending
- 1996-04-13 TW TW085104429A patent/TW318180B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996031495A1 (fr) | 1996-10-10 |
| EP0764646A4 (en) | 2001-08-08 |
| KR100211492B1 (ko) | 1999-08-02 |
| CN1149872A (zh) | 1997-05-14 |
| US5833813A (en) | 1998-11-10 |
| DE69628889D1 (de) | 2003-08-07 |
| EP0764646B1 (en) | 2003-07-02 |
| KR970703331A (ko) | 1997-07-03 |
| EP0764646A1 (en) | 1997-03-26 |
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